Asymmetric Induction on a Racemic Amine by Chiral Dipeptide 5(4H)-Oxazolones from C~(alpha)-Methyl Phenylglycine

摘要

Only remarkably complex, chiral, acylating reagents have been so far developed and tested for stereoselective acylation of racemic amines. In contrast, in this work we exploited a set of simple, chirally stable, N~(alpha)-acetylated, C~(alpha)-methyl phenylglycine [(alpha Me)Phg]-based dipeptide 5(4H)-oxazolones to check to which extent they might be able to differentiate between the two enantiomers of a primary amine (alpha-phenylethylamine) during amide bond formation. A typical example of the test system developed for this study is shown in Scheme 1.